Iron-catalyzed C-N bond formation via oxidative C-sp3-H bond functionalization adjacent to nitrogen in amides and anilines: Synthesis of N-alkyl and N-benzyl azoles

Iron catalyzed oxidative protocol was developed to couple azoles with amides to generate N-alkylazole derivatives in moderate to excellent yields using tertiarybutyl hydroperoxide as an oxidant under mild reaction conditions. Furthermore, this protocol explored to couple azoles with N-alkylanilines,...

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Bibliographic Details
Published inTetrahedron letters Vol. 56; no. 28; pp. 4200 - 4203
Main Authors Saidulu, G., Kumar, R. Arun, Reddy, K. Rajender
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 08.07.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Azole
ACTIVATION
Carbon-nitrogen bond
H BOND
TERTIARY-AMINES
Iron
HETEROCYCLIC CARBENES
Oxidative coupling
DEHYDROGENATIVE COUPLING REACTION
MOLECULAR DOCKING
VISIBLE-LIGHT
Peroxide
ANTIFUNGAL AGENTS
HYDROGEN-PEROXIDE
DERIVATIVES
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Summary:Iron catalyzed oxidative protocol was developed to couple azoles with amides to generate N-alkylazole derivatives in moderate to excellent yields using tertiarybutyl hydroperoxide as an oxidant under mild reaction conditions. Furthermore, this protocol explored to couple azoles with N-alkylanilines, unexpectedly N-benzyl azoles were obtained as major products under these oxidative conditions. (C) 2015 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2015.05.048